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Literature DB >> 12735778

The C2 selective nucleophilic substitution reactions of 2,3-epoxy alcohols mediated by trialkyl borates: the first endo-mode epoxide-opening reaction through an intramolecular metal chelate.

Minoru Sasaki¹, Keiji Tanino, Atsushi Hirai, Masaaki Miyashita.

Abstract

[reaction: see text] Highly efficient C2 selective substitution reactions of 2,3-epoxy alcohols with nucleophiles were developed by using NaN(3)-(CH(3)O)(3)B, NaSPh-(CH(3)O)(3)B, or NaCN-(C(2)H(5)O)(3)B system. The reaction proceeds through novel endo-mode epoxide opening of an intramolecular boron chelate, which was suggested from both experimental and quantum mechanic studies.

Entities: Chemical

Year: 2003 PMID： 12735778 DOI： 10.1021/ol034455f

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

9 in total

1. Asymmetric synthesis of diastereomeric diaminoheptanetetraols. A proposal for the configuration of (+)-zwittermicin a.

Authors: Evan W Rogers; Tadeusz F Molinski
Journal: Org Lett Date: 2007-02-01 Impact factor: 6.005

2. Tungsten-catalyzed regio- and enantioselective aminolysis of trans-2,3-epoxy alcohols: an entry to virtually enantiopure amino alcohols.

Authors: Chuan Wang; Hisashi Yamamoto
Journal: Angew Chem Int Ed Engl Date: 2014-10-19 Impact factor: 15.336

3. Synthesis of virtually enantiopure aminodiols with three adjacent stereogenic centers by epoxidation and ring-opening.

Authors: Lan Luo; Hisashi Yamamoto
Journal: Org Biomol Chem Date: 2015-10-06 Impact factor: 3.876

4. Synthesis of stereotetrads by regioselective cleavage of diastereomeric MEM-protected 2-methyl-3,4-epoxy alcohols with diethylpropynyl aluminum.

Authors: Wildeliz Torres; Gerardo Torres; José A Prieto
Journal: Synlett Date: 2012-10-01 Impact factor: 2.454

The C2 selective nucleophilic substitution reactions of 2,3-epoxy alcohols mediated by trialkyl borates: the first endo-mode epoxide-opening reaction through an intramolecular metal chelate.

1. Asymmetric synthesis of diastereomeric diaminoheptanetetraols. A proposal for the configuration of (+)-zwittermicin a.

2. Tungsten-catalyzed regio- and enantioselective aminolysis of trans-2,3-epoxy alcohols: an entry to virtually enantiopure amino alcohols.

3. Synthesis of virtually enantiopure aminodiols with three adjacent stereogenic centers by epoxidation and ring-opening.

4. Synthesis of stereotetrads by regioselective cleavage of diastereomeric MEM-protected 2-methyl-3,4-epoxy alcohols with diethylpropynyl aluminum.

5. (+)-Zwittermicin A. Rapid assembly of C9-C15 and a formal total synthesis.

6. Ring Opening of Epoxides by Pendant Silanols.

7. Synthesis of the C8'-epimeric thymine pyranosyl amino acid core of amipurimycin.

8. Tungsten-catalyzed regioselective and stereospecific ring opening of 2,3-epoxy alcohols and 2,3-epoxy sulfonamides.

Review 9. Chemistry and biology of bengamides and bengazoles, bioactive natural products from Jaspis sponges.